tagFirst TimeMy Chance with Cindy

My Chance with Cindy


After the football game I was beat. We had struggled but lost. I wanted so badly to go home with a win so we could have a reason to be proud. I put in my best, I knew it, the coach new it, my team mates knew it. But I could not shake the feeling of defeat.

So, when Cindy yelled for me to hurry and get in the car I half heartedly limped over towards the old Buick. There had to be seven kids in there already. Cindy looked over the door at me with her bottom lip pouted, "cheer up Lips, you played great".

Lips, what a retarded nickname. I wasn't sure where it came from exactly but at eighteen years old, I still could not shake it.

Cindy stepped away from the front passenger side door and said, "here... get in and I'll sit on your lap." I lowered my head and looked into the car. Craig was driving. Great... Craig was Cindy's boyfriend. The night was not getting any better.

I had a wild crush on Cindy. She was 20 years old, about 5'2" and 110 pounds soaking wet. She was a university Cheerleader and a senior. She had a very cute little body with perfect martini glass breasts that begged beneath her uniform. Her legs were slender but athletic. She had a heart shaped butt which her uniform accented perfectly. She was a brunette with lots of energy, a big smile, and bright eyes.

The thing about Cindy was that the whole room would look up when she walked in. But she barely knew I existed. I was a lowly second string player on the University team. Occasionally, the coach would let me play a first string position if he was short. And that is how I even bumped into Cindy's world.

I climbed into the Buick. Craig gave me that look and then said, "Dude, you played your heart out, it just wasn't our night." Cindy smiled and climbed in sitting her tiny body on my lap and wrestling the huge door closed.

We drove through the poorly lit desert back to our home town. I had a new problem. Cindy's cute little rump was positioned perfectly over my crotch. Each time we hit the slightest bump my penis was getting the full effect of driving itself between the perfect cheeks of her bottom. Well, as much as it could through the thick fabric of my warm up sweats.

I became very quiet wondering if Cindy had any clue what was actually going on. What was she thinking? How could she possibly ignore this growing problem? Cindy shifted slightly turning to look at me. She smiled but I pretended to be looking out the window at nothing.

The car drove past mile after mile of nothing. Cindy leaned her head closer to mine, brushing just the tip of her nose on my ear. She slowly began to blow in my ear. My body tensed and my lips began to grin just a tiny bit. I still looked out the window trying not to reveal my embarrassment.

Then Cindy whispered, "I can see that you are enjoying the ride. So am I. This is very nice." Then there was a long pause as she rubbed her nose on my ear very lightly, then she continued, " I wish we were alone. I think you are a sweet guy. Too bad I have a boyfriend right now." My heart was in my throat. I could not even think of anything to say.

I thought about pretending not to have heard anything she said. Everyone else in the car was being rowdy. Craig had the music turned way up. I wondered what I should do? Cindy had her elbow on top of my forearm. I moved my forearm off the armrest on the door and down to the space between the lower seat cushion and the door. Her tiny arm followed. My hand slowly and nervously found hers. I slid my fingers between hers. She just kind of let me do that. Her hand felt so soft and warm.

We continued to drive through the night. I was lost in this private exchange. Then Cindy moved her hand away from mine to her lap. I felt discouraged. She lifted herself a bit, moved her hips from side to side, grinding her cute bum onto my raging hard on. She pretended to be adjusting her skirt.

What she had really done was move the fabric of the skirt from between my raging hard on and her cute bum. Her hand returned to mine clasping it with our fingers interlocked. Now the only thing between my raging throbbing penis and her warm skin were the panties of her uniform and the material of my warm up sweat pants.

I laid my head on the back of the seat and up against the window. This was a rare moment and I knew it. Losing the game meant nothing now. Cindy turned her head towards Craig and asked, "are we going to the party at Wilson's?"

Craig turned down the radio, looked to the back seat and asked, "You guys want to go to Wilson's party?"

The back seat had three other University football players crunched in tightly and Stacy, another cheerleader kind of sprawled across them. They all had the game still in the forefront of their minds. In the front seat we had me, with Cindy sitting on my lap, another University player in the middle and then of course Craig who was driving his dad's piece of crap Buick. Nobody said anything.

I had wanted to ride my motorcycle to the game but the second string University players had to ride the bus, no ifs ands or buts. Since the coach asked me to plat first string, I was able to hitch a ride with Craig. I had no clue I would end up going to a party.

Cindy realized the dilemma I was in. She put her little hand on my chin, turned my head to face her and asked, "hey Lips, it's OK if you tag along with us to the party isn't it?"

I didn't know what to say. My folks were not the type that needed to know where I was every minute, but even though I was eighteen my dad would still always lock the front door at midnight. That way I had to wake him up and explain what I was doing if I got home after that. I did not even think it through, my mind was swimming with Cindy looking into my eyes and actually talking to me. I managed to speak, "Sure that sounds cool."

Cindy turned to the back seat to talk to Stacy. When she tuned her body, my raging boner adjusted a little. It was throbbing uncontrollably. I thought I was going to lose my load right there in my warm up sweats. Cindy must have felt something because she tensed her buttocks and squeezed my hand playfully. I was not sure how much more of this I was going to be able to take. I put my head back and looked out the window biting my bottom lip.

As we entered our little town, my heart sank a little. I realized the ride would be over soon. I thought I should do something, or say something before this magical moment was over. I could not think. My brain was mush. Besides what could I do without Craig knowing?

Just then, Craig pulled into the 7-11 abruptly and the old Buick bounded up and down. Cindy's head bounced off the headliner. "Craig you fuck! Slow down before you kill someone" Cindy yelled. I grinned, that bounce was fantastic. Cindy went up off my lap and then came right back down, right on my raging hard on. Plus her reaction kind of let me know where her relationship with Craig stood.

Another car pulled up alongside Craig's on the passenger side. Cindy rolled down the window and perched her whole upper body out the window. "We're going to Wilson's" she began talking to the driver in the other car which was also packed with people from our University.

With Cindy's upper body perched out of the window her fantastic bum was now displayed right in front of my face. Craig looked over at me, kind of catching me taking a long gander at the perfectly shaped ass. He smiled and put his finger up to his lips, signaling me to keep a secret.

Craig quickly reached over and grabbed Cindy's ass and returned his hand to the steering wheel just as quickly. Cindy lurched around and looked at me with a total look of amazement. "Hey Lips! Did you just grab my butt? Shame on you!" she said in a half hearted disapproving tone. As she said it, she looked out the corner of her eye at Craig, she was wondering if he had seen what just happened. She returned to leaning out the window.

Craig slapped the steering wheel smiling at me and laughed, "I like you Lips, you are one cool dude. Nothing ever trips you up does it?" I just shook my head in approval smiling. I wondered what Cindy must really be thinking about what just happened.

Craig looked at me and cocked his head up while looking at Cindy's ass, "Go ahead Lips... Get'er" I could not believe what I was hearing. Before my mind could think of the outcome, I nervously reached my left hand up and grabbed a handful of Cindy's amazing ass! My opened hand covered one whole cheek of her petite perfectly curved bottom.

Maybe my hand lingered to longingly, maybe my grab had a sense of sexuality instead of horseplay, but whatever it was, this time Cindy turned to both of us and said, "Ok I don't know which one of you keeps doing that but knock it off!" Then she turned back to the other car.

I knew that Cindy could tell that second grab was somehow different. I could feel her grip on my forearm had changed to something more sensual and gentle. Craig was laughing, "Lips, that's what I like about you man, you see a hole in the game and you go for it! No hesitation! No thought of the pain! You are something else dude!"

Craig must have felt some sense that I would not have the guts to do it. Was he crazy? What red blooded American male would pass up a freebie like that? He must have also felt the need to one up me because he reached his hand over to Cindy's ass and this time he grabbed her panties and jerked them up hard giving her a perfect wedgie! Holy Cow! Her cute cheerleader panties had all but disappeared between her picture perfect little ass cheeks!

The image of those bare perfect little ass cheeks was now emblazoned into my head like some kind of mental tattoo. My head was spinning. Cindy quickly pulled the panties back into place while yelling, "Craig you FUCK! Why are you being such a total ass?"

I knew why. Partly because he could. Craig was the captain of the University team, he could do anything. Plus, when an ass like that is perched so conveniently and Craig sees another guy looking at it, he has to do something to let that guy know who that ass belongs to.

Cindy sat back down and began to roll up the window. It felt good to feel those warm ass cheeks back on top of my hard raging cock. "They already have the beer. Go ahead and drive to Wilson's" Cindy said to Craig. Cindy was now sitting with her arms folded tightly. She then asked, "Craig was that my imagination? Or did Lips actually grab my ass?"

Craig just laughed and said, "Lips is his own man, and he's not afraid of anything. He sees an opportunity and he grabs it! That's why he's the man to throw the ball to, right Lips?" Ok, that part was true. I was always in the open. I would always catch the ball even if it meant getting totally clobbered. And clobbered was what I got all night long. My body felt like hamburger. I was sore from head to toe.

I felt like an idiot now. Why did Craig do that? Now what was I supposed to say? Before I could answer Cindy piped up in a quiet serious voice, "Lips, did you really grab my ass?"

Now the whole car was quiet. Everyone seemed to be wondering exactly how I was going to handle this, including me. I looked up at Cindy without smiling and said, "Cindy, you have such an incredible ass I could not help myself." And there was allot of truth in that statement.

A few guys in the back seat began to whoop it up, "Yeah Cindy! You can't blame Lips... that's some damn fine ass!" They were laughing and high fiving. This was not helping my cause. But I was glad for the comic relief. I wondered what she was thinking.

As we pulled into Wilson's long driveway, Cindy slid her right hand down to my leg and gave it a long hard squeeze. Then her hand stroked my thigh up and down almost lovingly. I put my hand on top of hers and gave it a loving squeeze. It was the best I could come up with. I really just wanted to wrap my arms around her tightly, but I knew that would be suicide.

The car came to a stop and Cindy flung the door open in a huff. She rammed her elbow into my chest in protest as she climbed out. "That's for grabbing my ass" she announced to the group. She about knocked the wind out of me. The guys in the back were laughing their asses off. Craig just looked at me and winked.

I knew this was going to be a dicey night. On the one hand, I knew I would be willing to risk getting a pounding from Craig if I got a chance to get it on with Cindy. On the other hand, I could sense that Cindy was very aware of my desires, but that she did not want to create a problem that would compromise her relationship with Craig.

As I got my aching, beat up, body out of the Buick I wondered what amazing things might transpire between now and when I would be returning to the Buick sometime later that night. There are times when a guy has to do what a guy has to do. I knew what I wanted more than anything was to hold Cindy in my arms, and I was pretty sure that's what she wanted too.

I walked up the steps to Wilson's front door behind the rest of the group with Craig. He looked over at me and smiled saying, "Hey Lips, no biggie dude. Just messin with ya!"

I knew what he meant. Sometimes things don't always turn out the way we hope they will. He thought he was being funny setting me up like that. I smiled and said, "Craig, you owe me one, OK?" And he knew he did. He owed me for more than what happened in the car. He owed me for taking all those sacks during the game, even after we knew we were losing. It made him look good.

"Sure Lips, I owe you one man! Count on it!" he replied putting his arm around my neck and pretending to take me down. I dug my shoulder into him with my arms around his waist and lifted him up off the ground, dropping him to his feet on the porch.

We walked into Wilson's house. The place was packed with people from our University. I walked over to the table and picked up a coke and a handful of peanuts. Then another, and another. After my third handful of nuts, Stacy came up and handed me a huge slice of one of the six foot hoagies they had in the kitchen.

Stacy smiled at me and said, "Hey, I think I'm onto you."

"Uh... what do you mean?" I replied.

Stacy looked up at me curiously and asked, "You have the hots for Cindy don't you?"

I looked down at my feet and then back up to meet Stacy's eyes and said, "Maybe I do, and maybe I don't, why do you ask?"

Stacy smiled really big and said, "Well if you do like her, I know Craig is going to be playing pool all night, like he always does. And Cindy is just sitting out behind the barn all by herself just staring at the moon."

"Woe dude! Are you serious?" I quickly snapped back accidentally revealing my interest.

Stacy smiled coyly and said in a whisper, "I would not run out there right away big fella, give it a minute... and then make your way out there. Finish your sandwich while we chat."

My brain was swimming. What did all this mean? I hardly even knew Stacy. And what I did know about her is that she followed Craig around like a lost puppy dog. Why was she doing this? Should I trust her? Was this some kind of setup like what just happened in the car?

I stumbled with my reply, "Uh, Stacy... that would be total suicide. Craig would pound me for sure if he found out."

Stacy placed her hand on my shoulder and leaned her mouth to my ear whispering, "I will keep my eye on Craig for you. If he even starts thinking of walking out there, I will flip the porch lights on."

"Is Cindy in on this?" I asked.

Stacy smiled and said giggling, "She told me about your ride out here, and she really wants to help you with that big problem you seem to have." Stacy looked down towards my crotch.

"She TOLD you about that!" I demanded.

Stacy got a serious look on her face, "We Cheerleaders have no secrets between us."

"REALLY..." I replied in total amazement. The whole thing was kind of freaking me out. Obviously, Cindy would have had to have told her something. There would be no other way for Stacy to know about that.

"She really thinks you're a sweet guy." Stacy added.

Now I knew they must have been talking, because that was what Cindy had whispered in my ear. This seemed too good to be true. My brain was quickly trying to assess the information I was being given, but it just was not adding up. At the same time, I knew this was a rare opportunity, and after seeing Cindy's perfectly shaped bare cheeks, feeling her little body sitting on my lap, those perky little breasts, the way she blew in my ear, interlocked her fingers with mine... I knew I had to take the chance.

I took a bite of the sandwich, a big bite. My heart was pounding. I spoke out of the side of my mouth while chowing down, "Stacy... I'm not sure what to do here... Do I just walk out there? What do I say?"

Stacy giggled, "Lips... you don't have to say anything. Just go out there and be with her. Whatever happens will just happen."

I took the last half of the sandwich and crammed it into my mouth. My heart felt like it was going to beat through my chest. I was breathing hard through my nostrils as I was chewing. My mind was numb. I could not make much sense out of what she was saying. I gulped hard and said, "So I could just walk out there and just kinda....sit next to her?"

Stacy smiled quietly and said in a serious voice, "Lips... you really are a sweet guy. Don't worry... you just do what feels right. You will be fine."

I drank the rest of my coke and crumpled the can, before tossing it across the room into the trash. Stacy took a napkin and wiped the mayonnaise from the corner of my mouth smiling. I smiled back at her with a wink and said, "Hey Stacy... Thanks for the sandwich."

I walked out to the room where Craig was playing pool with a few other team mates. They were well into it. They each had a beer in hand. They were high fiving each other. There was money on top of the stereo, they were playing for keeps. So was I.... apparently.

I looked up and saw Stacy enter the room. She pretended not to see me. I watched them play pool for another few minutes. My heart was pounding, my hands felt clammy. I took a deep breath and walked back through the house to the back porch. The lights were out and it was very dark. I could see the barn off in the distance.

I slid the glass door open enough to slip through and closed the door behind me. It was a warm night. The nearly full moon lit the yard enough for me to see the path through the yard. I walked quickly away from the house trying not to be seen. As I got closer to the barn, I slowed down nearly stopping. In the back of my mind I worried that when I stepped around the corner of the barn, there would be some kind of goofy surprise cooked up by the team.

But then I remembered the things Stacy had said. She just knew too much for this to be some kind of joke. Then my mind quickly turned to Cindy. If she really was there, what did that mean? What would I say? How would I act? What would I do?

There was no time for thinking now, I rounded the corner of the barn. I looked over alongside the barn and there was a small porch area with a bench swing. The swing was moving slowly back and forth. Cindy was sitting in the middle of it. I could see her dainty legs pushing on the ground beneath her to keep the swing slowly moving.

I took a deep breath and slowly walked closer. I stopped a few feet from the bench swing facing Cindy, standing right in front of her. I couldn't think of what to say! My mind went totally blank. I just stood there with my hands in my pockets looking right at her.

She looked up at me and smiled, "Hey Lips, you found me. Have a seat."

There was no possible way I could sit with the raging hard on I was experiencing. I opened my mouth nervously and this is what came out, "I can't sit."

Cindy stopped the swing with a surprised look and asked, "Did you get hurt tonight? Where does it hurt?"

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byRickyroma© 9 comments/ 122835 views/ 28 favorites

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